Synthesis and pharmacological screening: Sulfa derivatives of 2-pipecoline-bearing 1,3,4-oxadiazole core

• Published in: Russian Journal of Bioorganic Chemistry
• Main Author: Aziz-ur-Rehman; Arif A.; Abbasi M.A.; Siddiqui S.Z.; Rasool S.; Shah S.A.A.
• Format: Article
• Language: English
• Published: Maik Nauka Publishing / Springer SBM 2017
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85021450391&doi=10.1134%2fS1068162017030025&partnerID=40&md5=3eac25863f9bc97c4c1bf4915f182b67

An electrophile, 1-(4-(bromomethylbenzenesulfonyl)-2-methylpiperidine, was synthesized by the reaction of 2-methylpiperidine (2-pipecoline) and 4-bromomethylbenzenesulfonyl chloride in a weak basic medium under pH control. A series of nucleophiles, 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols, were synthesized from corresponding carboxylic acids in three steps. The title molecules were synthesized by coupling the electrophile to nucleophiles in an aprotic medium using LiH as an activator. The structures of all synthesized compounds were corroborated through IR, 1H NMR, and EI-MS techniques. All the compounds were screened for their pharmacological behavior, particularly, antibacterial and enzyme inhibitory activities. Notably efficient results were obtained against both gram-positive and gram-negative bacterial strains. Regarding enzyme inhibition, compounds were efficient against acetylcholinesterase and butyrylcholinesterase. © 2017, Pleiades Publishing, Ltd.